3-甲基-1,2,3,4-四氢异喹啉 | 29726-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 3-甲基-1,2,3,4-四氢异喹啉
• 英文名称: 3-Methyl-1,2,3,4-tetrahydroisoquinoline
• CAS: 29726-60-1
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: UEKQPSAKUNXFHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  3-甲基-1,2,3,4-四氢异喹啉 在 potassium tert-butylate 作用下， 以 邻二甲苯 为溶剂， 反应 36.0h， 以60%的产率得到3-甲基异喹啉
  参考文献：
  名称：

  叔丁醇钾促进的N-杂环无受体脱氢

  摘要：

  钾叔N-杂环的丁醇促进的acceptorless脱氢高效地实现用于N-杂芳烃和氢气的过渡金属-自由条件下产生。在存在KO t Bu碱的情况下，各种六元和五元N-杂环化合物可以有效地进行无受体脱氢，从而在140°C的邻二甲苯中提供相应的N-杂芳烃和H 2气体。本协议提供了一条通往芳香族含氮化合物和H 2气体的便捷途径。

  DOI：

  10.1002/adsc.201900499
• 作为产物：
  描述：

  (R)-3-甲基 3,4-二氢异喹啉盐酸盐 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以82.3%的产率得到3-甲基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  Conformational Analysis. 50. C-Methyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  Conformational equilibria in 1-, 3-, and 4-methyl-1,2,3,4-tetrahydroisoquinolines (THIQs) and the diastereomeric pairs of their 1,3- and 1,4-dimethyl homologs have been determined by measurement of H-3/H-4(trans) coupling constants and have been confirmed by molecular mechanics [MMP2(85]) calculations. The experimental -Delta G degrees values (a --> e) for the monomethyl compounds (computed values in parentheses) in kcal mol(-1) are Me-1, 0.56 (0.46); Me-3, 1.63 (1.53); and Me-4, -0.32 (-0.22). Agreement of experimental and calculated values is very goad as is the additivity of values for the dimethyl compounds (Table 1). Values for the corresponding hydrochlorides are Me-1, 0.19 (-0.34); Me-3, 1.15 (1.46); and Me-4, 0.35 (0.10) kcal mol(-1). The less than satisfactory agreement of experimental with computed data here is probably due to neglect of solvation. The very small or negative Delta G degrees values for Me-1 and Me-4 were ascribed not only to the pseudoaxial (rather than axial) nature of Me(ax) and the absence of a syn-axial hydrogen on the side of the benzene ring but also to a peri interaction with H(8) and H(5), respectively, destabilizing equatorial methyl at positions 1 and 4. This was confirmed by comparing computed conformational energy values with values at corresponding positions in Delta(3,4)-tetrahydropyridines (THPs). While Delta G degrees in the two series is the same for Me-3 (THIQ numbering), that for Me-1 and Me-4 is considerably smaller in the THIQ than in the THP series which latter is devoid of peri hydrogens.

  DOI：

  10.1021/jo971257r

文献信息

• COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE 4 POLYPEPTIDES
  申请人：Arvinas, Inc.

  公开号：US20190151295A1

  公开（公告）日：2019-05-23

  The present disclosure relates to bifunctional compounds, which find utility as modulators of Interleukin-1 Receptor-Associated Kinase 4 (IRAK-4); the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hppel-Lindau, cereblon, ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为白细胞介素-1受体相关激酶4（IRAK-4；目标蛋白）的调节剂具有实用性。具体而言，本公开涉及包含一端结合E3泛素连接酶的Von Hppel-Lindau、cereblon配体的双功能化合物，另一端结合目标蛋白的部分，使得目标蛋白靠近泛素连接酶以实现目标蛋白的降解（和抑制）。本公开展示了与目标蛋白的降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由目标蛋白聚集或积累导致的疾病或紊乱。
• The Remarkable Effect of a Simple Ion: Iodide-Promoted Transfer Hydrogenation of Heteroaromatics
  作者：Jianjun Wu、Chao Wang、Weijun Tang、Alan Pettman、Jianliang Xiao

  DOI：10.1002/chem.201201517

  日期：2012.7.27

  I can do it! Accelerated by simple iodide ions, rhodium‐catalysed transfer hydrogenation can be readily performed on quinolines, isoquinolines and quinoxalines, affording the tetrahydro products in high yields with low catalyst loading (see scheme).

  我能做到！通过简单的碘离子加速，铑催化的转移加氢反应可轻松地在喹啉，异喹啉和喹喔啉上进行，从而以高收率和低催化剂负载量提供四氢产物（参见方案）。
• Indium as a Reducing Agent: Selective Reduction of the Heterocyclic Rings in Quinolines, Isoquinolines and Quinoxalines
  作者：Christopher J. Moody、Michael R. Pitts

  DOI：10.1055/s-1998-1836

  日期：1998.9

  The heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanol.

  在水中乙醇溶液中，使用金属铟对喹啉、异喹啉和喹喔啉中的杂环进行选择性还原。
• Novel and Facile Reduction of Heterocyclic Compounds with Lanthanoid Metal-Hydrochloric Acid System.
  作者：Yasuko KAMOCHI、Tadahiro KUDO

  DOI：10.1248/cpb.43.1422

  日期：——

  Pyridines were rapidly reduced to piperidines with Sm or Yb-HCl system at room temperature in quantitative yields. Quinolines and isoquinolines were similarly reduced to the corresponding 1, 2, 3, 4-tetrahydro-derivatives with Sm-HCl system in good yields.

  吡啶类化合物在室温下通过Sm或Yb-HCl体系迅速还原为哌啶类化合物，产率定量。喹啉和异喹啉同样通过Sm-HCl体系被还原为对应的1,2,3,4-四氢衍生物，产率良好。
• [EN] SUBSTITUTED SULFONAMIDES USEFUL AS ANTIAPOPTOTIC BCL INHIBITORS<br/>[FR] SULFONAMIDES SUBSTITUÉS UTILES COMME INHIBITEURS DE BCL ANTI-APOPTOTIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012162365A1

  公开（公告）日：2012-11-29

  Disclosed are compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein: W and Q and G are defined herein. Also disclosed are methods of using such compounds as inhibitors of Bcl-2 family antiapoptotic proteins for the treatment of cancer; and pharmaceutical compositions comprising such compounds.

  揭示了式（I）的化合物或其药学上可接受的盐，其中：W、Q和G在此处被定义。还揭示了将这些化合物用作Bcl-2家族抗凋亡蛋白的抑制剂以治疗癌症的方法；以及包含这些化合物的药物组合物。